Through a social constructivist lens, this study looked at how paraprofessionals understand mathematics instructional content and associated pedagogical skills and explore an organization's current involvement of support staff in schools' mathematical classrooms. The setting for this bounded case study was two elementary schools contained in one rural district of Massachusetts, with paraprofessionals' involvement in math instruction in kindergarten through sixth grade as the focal point. Data was collected by documentation, demographic surveys, qualitative open-ended surveys, and focus groups. Thirty-two individuals within the organization qualified to participate in this study. A total of 22 documents and ten qualitative open-ended surveys were analyzed. Four participants served as members of the focus groups. The theoretical framework of role theory and self-efficacy theory highlighted participant insight of how these areas related to their work and daily motivation in an elementary mathematics classroom. The findings of data collection resulted in themes of value, confidence, and actualized roles. This study led to promoting needs of support staff, increased conversations, collaboration in regard to job roles, and a need for clearer utilization of support staff to strengthen mathematics instruction in the classroom. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]